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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 06:54:47 UTC

Update Date

2021-09-24 06:54:48 UTC

HMDB ID

HMDB0304071

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-hydroxyisoflavanone naringenin

Description

2-hydroxyisoflavanone naringenin, also known as 2,5,7,4'-tetrahydroxyisoflavanol or 2-hydroxy-2,3-dihydrogenistein, is a member of the class of compounds known as isoflavanols. Isoflavanols are polycyclic compounds containing a hydroxylated isoflavan skeleton. 2-hydroxyisoflavanone naringenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-hydroxyisoflavanone naringenin can be found in a number of food items such as wild carrot, chicory, cloves, and sweet cherry, which makes 2-hydroxyisoflavanone naringenin a potential biomarker for the consumption of these food products.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0304071
     RDKit          3D
2-hydroxyisoflavanone naringenin
 33 35  0  0  0  0  0  0  0  0999 V2000
    0.0778   -1.9030   -0.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4701   -0.7354    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8794   -0.4134   -0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695   -1.3769   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4824   -2.6981    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1804   -0.9722   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335    0.3717   -0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8734    0.6804   -0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    1.2992   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090    0.9273   -0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2270    1.8984   -0.1466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452    1.6202   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    2.6594    0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4526    0.3585    0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -0.0264    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833   -0.3721   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7170   -0.7290   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884   -0.7538    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9205   -1.1165   -0.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0801   -0.4079    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7555   -0.0540    1.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1782   -3.4305    0.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9360   -1.7427   -0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1267    1.6600   -0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926    2.3382   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    1.5466   -1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260    2.8042    1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2304    0.6028    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -0.3784   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1370   -1.0059   -2.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6397   -0.4388   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7580   -0.4265    2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653    0.2149    2.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 14  2  1  0
 21 15  1  0
 10  3  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  END


  Mrv1533004251506532D          

 21 23  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304071

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1OC2=CC(O)=CC(O)=C2C(=O)C1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O6/c16-8-3-1-7(2-4-8)12-14(19)13-10(18)5-9(17)6-11(13)21-15(12)20/h1-6,12,15-18,20H

> <INCHI_KEY>
UQOJAGBSKPHQOG-UHFFFAOYSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.255

> <EXACT_MASS>
288.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.85276440823327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,7-trihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
2.363434172333333

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.169294083894586

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.79347091958811

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2559145364515425

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
72.70640000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2,3-dihydrogenistein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304071
     RDKit          3D
2-hydroxyisoflavanone naringenin
 33 35  0  0  0  0  0  0  0  0999 V2000
    0.0778   -1.9030   -0.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4701   -0.7354    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8794   -0.4134   -0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695   -1.3769   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4824   -2.6981    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1804   -0.9722   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335    0.3717   -0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8734    0.6804   -0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    1.2992   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090    0.9273   -0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2270    1.8984   -0.1466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452    1.6202   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    2.6594    0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4526    0.3585    0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -0.0264    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833   -0.3721   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7170   -0.7290   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884   -0.7538    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9205   -1.1165   -0.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0801   -0.4079    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7555   -0.0540    1.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1782   -3.4305    0.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9360   -1.7427   -0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1267    1.6600   -0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926    2.3382   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    1.5466   -1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260    2.8042    1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2304    0.6028    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -0.3784   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1370   -1.0059   -2.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6397   -0.4388   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7580   -0.4265    2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653    0.2149    2.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 14  2  1  0
 21 15  1  0
 10  3  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    2   15                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0304071
HETATM    1  O1  UNL     1       0.078  -1.903  -0.085  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.470  -0.735   0.110  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.879  -0.413  -0.030  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.869  -1.377  -0.041  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.482  -2.698   0.088  1.00  0.00           O  
HETATM    6  C4  UNL     1       4.180  -0.972  -0.180  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.533   0.372  -0.308  1.00  0.00           C  
HETATM    8  O3  UNL     1       5.873   0.680  -0.442  1.00  0.00           O  
HETATM    9  C6  UNL     1       3.523   1.299  -0.293  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.209   0.927  -0.156  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.227   1.898  -0.147  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.145   1.620  -0.298  1.00  0.00           C  
HETATM   13  O5  UNL     1      -0.836   2.659   0.349  1.00  0.00           O  
HETATM   14  C9  UNL     1      -0.453   0.358   0.485  1.00  0.00           C  
HETATM   15  C10 UNL     1      -1.876  -0.026   0.308  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.383  -0.372  -0.926  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.717  -0.729  -1.073  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.588  -0.754   0.001  1.00  0.00           C  
HETATM   19  O6  UNL     1      -5.920  -1.116  -0.179  1.00  0.00           O  
HETATM   20  C14 UNL     1      -4.080  -0.408   1.234  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.756  -0.054   1.376  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.178  -3.431   0.084  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.936  -1.743  -0.186  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.127   1.660  -0.535  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.793   2.338  -0.391  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.371   1.547  -1.359  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.326   2.804   1.207  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.230   0.603   1.550  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.776  -0.378  -1.806  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.137  -1.006  -2.041  1.00  0.00           H  
HETATM   31  H10 UNL     1      -6.640  -0.439  -0.395  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.758  -0.426   2.073  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.365   0.215   2.342  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   14
CONECT    3    4    4   10
CONECT    4    5    6
CONECT    5   22
CONECT    6    7    7   23
CONECT    7    8    9
CONECT    8   24
CONECT    9   10   10   25
CONECT   10   11
CONECT   11   12
CONECT   12   13   14   26
CONECT   13   27
CONECT   14   15   28
CONECT   15   16   16   21
CONECT   16   17   29
CONECT   17   18   18   30
CONECT   18   19   20
CONECT   19   31
CONECT   20   21   21   32
CONECT   21   33
END

HMDB0304071
     RDKit          3D
2-hydroxyisoflavanone naringenin
 33 35  0  0  0  0  0  0  0  0999 V2000
    0.0778   -1.9030   -0.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4701   -0.7354    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8794   -0.4134   -0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695   -1.3769   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4824   -2.6981    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1804   -0.9722   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335    0.3717   -0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8734    0.6804   -0.4417 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5229    1.2992   -0.2926 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090    0.9273   -0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2270    1.8984   -0.1466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1452    1.6202   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    2.6594    0.3489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4526    0.3585    0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -0.0264    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833   -0.3721   -0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7170   -0.7290   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5884   -0.7538    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9205   -1.1165   -0.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0801   -0.4079    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7555   -0.0540    1.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1782   -3.4305    0.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9360   -1.7427   -0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1267    1.6600   -0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7926    2.3382   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    1.5466   -1.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3260    2.8042    1.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2304    0.6028    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -0.3784   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1370   -1.0059   -2.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6397   -0.4388   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7580   -0.4265    2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653    0.2149    2.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 14  2  1  0
 21 15  1  0
 10  3  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,5,7,4'-Tetrahydroxyisoflavanol	ChEBI
2,4',5,7-Tetrahydroxyisoflavanone	Kegg

Chemical Formula

C₁₅H₁₂O₆

Average Molecular Weight

288.255

Monoisotopic Molecular Weight

288.063388106

IUPAC Name

2,5,7-trihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

2-hydroxy-2,3-dihydrogenistein

CAS Registry Number

Not Available

SMILES

OC1OC2=CC(O)=CC(O)=C2C(=O)C1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H12O6/c16-8-3-1-7(2-4-8)12-14(19)13-10(18)5-9(17)6-11(13)21-15(12)20/h1-6,12,15-18,20H

InChI Key

UQOJAGBSKPHQOG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanols

Alternative Parents

Substituents

2-hydroxyisoflavanone
Hydroxyisoflavonoid
Isoflavanol
Isoflavanone
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Hemiacetal
Ketone
Polyol
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavanone (CHEBI:31080 )
isoflavanones (C12631 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.22	ALOGPS
logP	2.36	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.79	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.71 m³·mol⁻¹	ChemAxon
Polarizability	27.85 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	166.2	32859911
AllCCS	[M+H-H2O]+	162.488	32859911
AllCCS	[M+Na]+	170.637	32859911
AllCCS	[M+NH4]+	169.646	32859911
AllCCS	[M-H]-	165.887	32859911
AllCCS	[M+Na-2H]-	165.265	32859911
AllCCS	[M+HCOO]-	164.711	32859911
DeepCCS	[M+H]+	165.197	30932474
DeepCCS	[M-H]-	162.838	30932474
DeepCCS	[M-2H]-	195.724	30932474
DeepCCS	[M+Na]+	171.29	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 10V, Positive-QTOF	splash10-000i-0190000000-24a8178e44dac397196d	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 20V, Positive-QTOF	splash10-0pi9-0690000000-fd5cb04563ed14509976	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 40V, Positive-QTOF	splash10-0pdr-2920000000-265e556334b3bf7bd1fd	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 10V, Positive-QTOF	splash10-000i-0190000000-24a8178e44dac397196d	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 20V, Positive-QTOF	splash10-0pi9-0690000000-fd5cb04563ed14509976	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 40V, Positive-QTOF	splash10-0pdr-2920000000-265e556334b3bf7bd1fd	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 10V, Negative-QTOF	splash10-000f-0190000000-5ee513272608d1c4ae5e	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 20V, Negative-QTOF	splash10-0f7c-0980000000-ded7c7c2e1ad2f1d341b	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 40V, Negative-QTOF	splash10-0a5l-4910000000-189bfb9e207a88a56acd	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 10V, Negative-QTOF	splash10-000f-0190000000-5ee513272608d1c4ae5e	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 20V, Negative-QTOF	splash10-0f7c-0980000000-ded7c7c2e1ad2f1d341b	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 40V, Negative-QTOF	splash10-0a5l-4910000000-189bfb9e207a88a56acd	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 10V, Negative-QTOF	splash10-000i-0090000000-d4a2ab999b513adc4185	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 20V, Negative-QTOF	splash10-000i-0970000000-c52953b55611240278f3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 40V, Negative-QTOF	splash10-05nf-7940000000-79995366c88ed16be045	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 10V, Positive-QTOF	splash10-0079-0090000000-cc646d677a2756f69c77	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 20V, Positive-QTOF	splash10-0f79-0930000000-1bb12ed19e2439720917	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-hydroxyisoflavanone naringenin 40V, Positive-QTOF	splash10-0a4i-4910000000-0bc08be2c0c98b1ea1ec	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030335

KNApSAcK ID

Not Available

Chemspider ID

391978

KEGG Compound ID

C12631

BioCyc ID

CPD-3161

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

31080

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2-hydroxyisoflavanone naringenin (HMDB0304071)

MOL for HMDB0304071 (2-hydroxyisoflavanone naringenin)

3D MOL for HMDB0304071 (2-hydroxyisoflavanone naringenin)

3D SDF for HMDB0304071 (2-hydroxyisoflavanone naringenin)

3D-SDF for HMDB0304071 (2-hydroxyisoflavanone naringenin)

PDB for HMDB0304071 (2-hydroxyisoflavanone naringenin)

3D PDB for HMDB0304071 (2-hydroxyisoflavanone naringenin)

SMILES for HMDB0304071 (2-hydroxyisoflavanone naringenin)

INCHI for HMDB0304071 (2-hydroxyisoflavanone naringenin)

Structure for HMDB0304071 (2-hydroxyisoflavanone naringenin)

3D Structure for HMDB0304071 (2-hydroxyisoflavanone naringenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra